30 days in Kentucky Itinerary

30 days in Kentucky Itinerary

Created using Inspirock Kentucky tour planner
Make it your trip
Drive
1
Lexington
— 8 nights
Drive
2
Louisville
— 8 nights
Drive
3
Cave City
— 6 nights
Drive
4
Hopkinsville
— 3 nights
Drive
5
Paducah
— 4 nights
Fly

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Lexington — 8 nights

Known internationally as the "Horse Capital of the World," Lexington boasts a thriving economy resting largely on its thoroughbred racehorse industry.
You'll explore the less-touristy side of things at Mary Todd Lincoln House and Red River Gorge Geological Area. Change things up with these side-trips from Lexington: Natural Bridge State Resort Park (in Slade), The Great American Dollhouse Museum (in Danville) and Shaker Village of Pleasant Hill (in Harrodsburg). There's lots more to do: gain some tasty knowledge on a distillery tour, brush up on your knowledge of spirits at Castle & Key Distillery, examine the collection at Aviation Museum of Kentucky, and relax and rejuvenate at some of the best spas.

To see ratings, maps, and tourist information, go to the Lexington trip planner.

Columbus to Lexington is an approximately 3-hour car ride. You can also take a bus; or fly. In November, daily temperatures in Lexington can reach 56°F, while at night they dip to 36°F. Wrap up your sightseeing on the 9th (Tue) to allow time to drive to Louisville.
Historic Sites · Breweries & Distilleries · Museums · Parks
Side Trips

Louisville — 8 nights

Kentucky’s largest city, Louisville, is best known as the home of the Kentucky Derby.
Step off the beaten path and head to Conrad-Caldwell House Museum (Conrad's Castle) and Cave Hill Cemetery. Venture out of the city with trips to Bardstown (Old Bardstown Village Civil War Museum, Willett Distilling Company, &more) and Bernheim Arboretum & Forest (in Clermont). Next up on the itinerary: stroll around Cherokee Park, get thoroughly spooked out with a ghost and vampire tour, see the interesting displays at Frazier History Museum, and sample the fine beverages at Kentucky Peerless Distilling Co.

Planning Louisville trip won't be overwhelming when you use Inspirock's itinerary maker.

Drive from Lexington to Louisville in 1.5 hours. Alternatively, you can take a bus. In November, daytime highs in Louisville are 57°F, while nighttime lows are 37°F. Finish up your sightseeing early on the 17th (Wed) so you can go by car to Cave City.
Breweries & Distilleries · Parks · Museums · Historic Sites
Side Trips

Cave City — 6 nights

Originally intended as a resort city to serve the Mammoth Cave attraction, Cave City has taken on a life of its own.
You'll explore the less-touristy side of things at Limestone Branch Distillery and Cub Run Cave. Venture out of the city with trips to Elizabethtown (Freeman Lake Park & Swope's Cars of Yesteryear Museum) and Abraham Lincoln Birthplace National Historical Park (in Hodgenville). And it doesn't end there: surround yourself with nature on a nature and wildlife tour, Head underground at Diamond Caverns, admire nature's wide array of creatures at Kentucky Down Under Adventure Zoo, and see the interesting displays at Dinosaur World.

To find photos, other places to visit, traveler tips, and more tourist information, read our Cave City sightseeing planning website.

Traveling by car from Louisville to Cave City takes 1.5 hours. Alternatively, you can do a combination of bus and car; or do a combination of bus and taxi. Due to the time zone difference, you'll gain 1 hour traveling from Louisville to Cave City. In November, daily temperatures in Cave City can reach 57°F, while at night they dip to 36°F. Finish your sightseeing early on the 23rd (Tue) so you can travel to Hopkinsville.
Parks · Nature · Museums · Outdoors
Side Trips

Hopkinsville — 3 nights

Hopkinsville is a home rule-class city in and the county seat of Christian County, Kentucky, United States. You'll explore the less-touristy side of things at Casey Jones Distillery and Smothers Park. You'll find plenty of places to visit near Hopkinsville: Woodlands Nature Station (in Cadiz) and Land Between the Lakes NRA, Golden Pond Visitor Center & Planetarium (in Golden Pond). There's still lots to do: contemplate the long history of Jefferson Davis State Historic Site.

For photos, reviews, traveler tips, and more tourist information, read Hopkinsville trip planning website.

Getting from Cave City to Hopkinsville by car takes about 2 hours. In November, daytime highs in Hopkinsville are 58°F, while nighttime lows are 38°F. Finish up your sightseeing early on the 26th (Fri) so you can go by car to Paducah.
Parks · Wildlife · Breweries & Distilleries · Historic Sites
Side Trips

Paducah — 4 nights

Paducah is a home rule-class city in and the county seat of McCracken County, Kentucky, United States. Discover out-of-the-way places like Purple Toad Winery and Bob Noble Park. Go for a jaunt from Paducah to Henderson to see Audubon State Park about 1h 45 min away. There's still lots to do: take a leisurely stroll along Paducah Riverwalk, admire the engineering at Kentucky Dam, contemplate the long history of Apple Valley Hillbilly Garden and Toyland, and have fun and explore at River Discovery Center.

To see more things to do, maps, photos, and other tourist information, go to the Paducah travel route builder site.

Getting from Hopkinsville to Paducah by car takes about 1.5 hours. November in Paducah sees daily highs of 59°F and lows of 37°F at night. Finish your sightseeing early on the 30th (Tue) to allow enough time to fly back home.
Parks · Historic Sites · Childrens Museums · Wineries
Side Trips

Kentucky travel guide

4.6
Caves · Distilleries · Specialty Museums
The Bluegrass State
A diverse region of sprawling farmland and rich cultural heritage, Kentucky is the birthplace of American horse racing and home to the world-famous Kentucky Derby. While the cities of Lexington and Louisville experience the majority of the state's tourism, Kentucky is also a favorite among outdoor enthusiasts with its array of natural attractions, including the Cumberland Gap and the world's longest cave system at Mammoth Cave National Park. Take a tour through original Civil War battlefields to delve into the nation's history, or head to one of the many bourbon distilleries to learn more about Kentucky's most famous export.